2-[(2R,4aR,6R,7R,8R,8aS)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-malonic acid dimethyl ester | 176755-68-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(2R,4aR,6R,7R,8R,8aS)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-malonic acid dimethyl ester
• CAS: 176755-68-3
• 化学式: C₂₂H₂₃N₃O₁₁
• 分子量: 505.438
• InChiKey: FGUHMBKBQAFMMP-NCOBNINSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  178.29
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-[(2R,4aR,6R,7R,8R,8aS)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-malonic acid dimethyl ester 在 水 、 三氟乙酸 作用下， 反应 3.0h， 以72%的产率得到dimethyl 2-[(2R,3R,4R,5S,6R)-2-(2,4-dioxopyrimidin-1-yl)-5-hydroxy-6-(hydroxymethyl)-4-nitrooxan-3-yl]propanedioate
  参考文献：
  名称：

  Stereoselective Reactions OF 1-(4,6-O-Benzylidene-2,3-Didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil with some Nucleophiles¶

  摘要：

  Michael addition of benzylamine, piperidine, morpholine, pyrrolidine, cyclohexylamine, allylamine and dimethylmalonate to the nitroolefin (5) generated in situ from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)uracil (4b) gave the corresponding 2-(substituted-amino)-3-deoxy-3-nitro-beta-D-glucopyranosides (6a-f and 6h). Reaction of 4b with N,N'-carbonyldiimidazole directly gave 6g. Compound 4b was converted into the 2-deoxy analogue (8), which was reduced to the 3-amino (9) and 3-hydroxylamino analogue (10).

  DOI：

  10.1080/07328319608002131
• 作为产物：
  描述：

  在 甲基磺酰氯 、 三乙胺 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2-[(2R,4aR,6R,7R,8R,8aS)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-malonic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective Reactions OF 1-(4,6-O-Benzylidene-2,3-Didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil with some Nucleophiles¶

  摘要：

  Michael addition of benzylamine, piperidine, morpholine, pyrrolidine, cyclohexylamine, allylamine and dimethylmalonate to the nitroolefin (5) generated in situ from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)uracil (4b) gave the corresponding 2-(substituted-amino)-3-deoxy-3-nitro-beta-D-glucopyranosides (6a-f and 6h). Reaction of 4b with N,N'-carbonyldiimidazole directly gave 6g. Compound 4b was converted into the 2-deoxy analogue (8), which was reduced to the 3-amino (9) and 3-hydroxylamino analogue (10).

  DOI：

  10.1080/07328319608002131